Boron tribromide → HCID 22004810, compound

HRID 324626Notes

Reaction equation

HRID 324626 reaction equation
[NH2:1][C:2]1[C:3]([O:17]C)=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:8][CH2:7]2.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:3]([OH:17])=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22004803HCID 22004803, compound

Product 1

HCID 22004810HCID 22004810, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(7-amino-6-methoxyindan-1-yl) ethyl]acetamide (1.1 g, 4.4 mmol.) in dichloromethane (20 mL) was added dropwise gradually boron tribromide (2.1 mL, 22.1 mmol.). The mixture was stirred for 30 minutes at the same temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with 10% methanol/chloroform. The extract solution was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1) to afford N-[2-(7-amino-6-hydroxyindan-1yl)ethyl]acetamide (yield 630 mg, 61%). A portion of the product was dissolved in ethanol, to which was added a saturated hydrochloric acid/ethanol solution. The solvent was distilled off under reduced pressure. The resulting crystalline precipitate was recrystallized from ethanol to afford the title compound.

Workup

  1. extractionwas subjected to extraction with 10% methanol/chloroform
  2. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-b8f16102cc064d28bc62824698997f9c
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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